Trimethylsilyl triflate → HCID 86704189, compound
Reaction equation
[C:1]([C:4]1[C:5]([F:25])=[C:6]([N:10]([CH2:22][O:23][CH3:24])[S:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH3:26][Si:27](OS(C(F)(F)F)(=O)=O)([CH3:29])[CH3:28]>C(Cl)Cl>[F:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[S:11]([N:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([O:3][Si:27]([CH3:29])([CH3:28])[CH3:26])=[CH2:2])[C:5]=1[F:25])[CH2:22][O:23][CH3:24])(=[O:13])=[O:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
100 mg (0.27 mmol) of N-(3-acetyl-2-fluorophenyl)-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide were dissolved in 4 mL of dry DCM under nitrogen atmosphere. The solution was cooled to 0° C. and 94 μL (0.65 mmol) of TEA and 106 μL (0.54 mmol) of trimethylsilyl-trifluoromethansulfonate were added. The solution was stirred 15 min at the same temperature and then diluted with DCM and washed rapidly with brine. The organic layer was dried over Na2SO4 and evaporated giving 2,5-difluoro-N-(2-fluoro-3-{1-[(trimethylsilyl)oxy]ethenyl}phenyl)-N-(methoxymethyl)benzenesulfonamide as a clear oil. The latter was re-dissolved in 4 mL of dry DCM under nitrogen atmosphere and 58 mg (0.32 mmol) of N-bromosuccinimide were added at 0° C. After 30 min the reaction was complete. The mixture was diluted with DCM and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and evaporated to give the title compound, which was used without any further purification.
Workup
- washwashed rapidly with brine
- dry with materialThe organic layer was dried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-87ba6c02d857434d97347195de41aa27
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199979B2
Reaction notes
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